Diisopropylethylamine → 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide

HRID 2283474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283474
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=O)[CH:3]=1.Cl.[CH:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[CH3:23])([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([CH:13]([CH3:14])[CH3:15])=[C:17]([CH3:23])[CH:18]=2)=[O:10])[CH:3]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27962704-Isopropyl-m-toluidinium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12828947Methyl 4-bromopicolinate

Produkt 1

HCID 1182507534-bromo-N-(4-isopropyl-3-methylphenyl)picolinamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-bromopicolinate (1.0 g, 5.0 mmol) in DCM (500 mL) and DMF (20 mL) was added 4-isopropyl-3-methylbenzenamine hydrochloride (1.08 g, 5.90 mmol), HATU (3.8 g, 10 mmol), DIPEA (4.9 mL, 30 mmol) and the mixture was stirred at reflux overnight. After cooling to room temperature and evaporation of the solvent, the residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate) to afford 4-bromo-N-(4-isopropyl-3-methylphenyl)picolinamide (1.32 g, 80% yield) as a yellow oil: MS (ES) m/z 333 (M+H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. customevaporation of the solvent
  3. customthe residue was purified by combi-flash (ISCO, 40g silica, UV254, 3:1 pet ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f777dd1fb7934bd5871f4b96b378eeb3
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145393B2

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